Synthesis of Chiral Assembly from Achiral Octadehydrotribenzo[14]annulene Derivative by Using a Twofold Helical Hydrogen-Bonding Template

Dedicated to Professor K. Peter C. Vollhardt

Abstract

Chiral supramolecular architecture was synthesized from the achiral noncentrosymmetric title compound by using a twofold helical hydrogen-bonding network as a template.

Key words

annulenes - macrocycles - carboxylic acid - chirality - supramolecular chemistry

• References and Notes

• 1 Present address: The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
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A handful of chiral assemblies based on [n]DBA were reported so far. For 2D assemblies based on hexadehydrotribenzo[12]annulene:
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For chiral crystal of octadehydrodibenzo[12]annulene:
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• 17 The obtained crystalline system is a conglomerate.
• 18 Procedure to Obtain a Single Crystal of 3·(t-BuNH₃)₂ 3H₂ (1 equiv) and tert-butylamine (1 equiv) was mixed in MeOH. The solvent was removed by evaporation, and the resulting white solid was dissolved in a mixed solvent of MeOH and 1,4-dioxane, followed by evaporated slowly at r.t. (20 °C) to give needle-like crystals suitable for X-ray crystallographic analysis.
• 19 Crystal Data for 3·(n-BuNH₃)₂ C₃₆H₃₄N₂O₄, Mw = 558.68, a = 29.6135(5) Å, b = 10.68715(19) Å, c = 19.5181(4) Å, α = 90° β = 90.9730(7)°, γ = 90°, V = 6176.29(19) ų, T = 213 K, monoclinic, space group P2₁/c (No. 14), Z = 8, d _calcd = 1.202 g/cm³, 68820 collected, 11107 unique (R _int = 0.043) reflections, the final R1 and wR2 values 0.069 [I > 2.0σ(I)] and 0.243 (all data), respectively. Crystal Data for 3·(t-BuNH₃)₂ C₃₆H₃₄N₂O₄, Mw = 558.68, a = 6.19060(10) b = 21.1236(4) Å, c = 23.5303(5) Å, α = β = γ = 90°, V = 3077.00(10) ų, T = 213 K, orthorhombic, space group P2₁2₁2₁ (no. 19), Z = 4, d _calcd = 1.206 g/cm³, 21962 collected, 3169 unique (R _int = 0.064) reflections, the final R1 and wR2 values 0.055 [I > 2.0σ(I)] and 0.152 (all data), respectively. CCDC-1051809 [3·(n-BuNH₃)₂] and 1051810 [3·(t-BuNH₃)₂] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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